AU731841B2 - Powder coated with sparingly soluble ultraviolet light absorber - Google Patents
Powder coated with sparingly soluble ultraviolet light absorber Download PDFInfo
- Publication number
- AU731841B2 AU731841B2 AU41359/97A AU4135997A AU731841B2 AU 731841 B2 AU731841 B2 AU 731841B2 AU 41359/97 A AU41359/97 A AU 41359/97A AU 4135997 A AU4135997 A AU 4135997A AU 731841 B2 AU731841 B2 AU 731841B2
- Authority
- AU
- Australia
- Prior art keywords
- ultraviolet light
- powder
- light absorber
- sparingly soluble
- soluble ultraviolet
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000000843 powder Substances 0.000 title claims description 106
- 229940124543 ultraviolet light absorber Drugs 0.000 title claims description 50
- 239000006097 ultraviolet radiation absorber Substances 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 claims description 48
- 241000565347 Pongamia Species 0.000 claims description 28
- 239000002537 cosmetic Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- IHWPQGIYXJKCOV-PTNGSMBKSA-N (z)-3-hydroxy-1-(4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one Chemical compound C1=CC=2OC=CC=2C(OC)=C1C(=O)\C=C(/O)C1=CC=CC=C1 IHWPQGIYXJKCOV-PTNGSMBKSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- IHWPQGIYXJKCOV-UHFFFAOYSA-N pongamol Natural products C1=CC=2OC=CC=2C(OC)=C1C(=O)C=C(O)C1=CC=CC=C1 IHWPQGIYXJKCOV-UHFFFAOYSA-N 0.000 claims description 5
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 claims description 2
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- GVSPXQVUXHMUMA-MDWZMJQESA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GVSPXQVUXHMUMA-MDWZMJQESA-N 0.000 claims 3
- VTCQGRUUIXLBJY-UHFFFAOYSA-N 2-ethylhexyl 3-[4-[(3,4-dimethoxyphenyl)methylidene]-2,5-dioxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OCC(CC)CCCC)C(=O)NC1=CC1=CC=C(OC)C(OC)=C1 VTCQGRUUIXLBJY-UHFFFAOYSA-N 0.000 claims 2
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- 238000000338 in vitro Methods 0.000 description 19
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- 229920005989 resin Polymers 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229920001214 Polysorbate 60 Polymers 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 235000013869 carnauba wax Nutrition 0.000 description 4
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- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 4
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 4
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- 239000010936 titanium Substances 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 3
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- 238000002834 transmittance Methods 0.000 description 3
- DGSZGZSCHSQXFV-UHFFFAOYSA-N 2,3-bis(2-ethylhexanoyloxy)propyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC(OC(=O)C(CC)CCCC)COC(=O)C(CC)CCCC DGSZGZSCHSQXFV-UHFFFAOYSA-N 0.000 description 2
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 2
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
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- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- DWMMZQMXUWUJME-UHFFFAOYSA-N hexadecyl octanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC DWMMZQMXUWUJME-UHFFFAOYSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- TVRGPOFMYCMNRB-UHFFFAOYSA-N quinizarine green ss Chemical compound C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1 TVRGPOFMYCMNRB-UHFFFAOYSA-N 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- UUJLHYCIMQOUKC-UHFFFAOYSA-N trimethyl-[oxo(trimethylsilylperoxy)silyl]peroxysilane Chemical compound C[Si](C)(C)OO[Si](=O)OO[Si](C)(C)C UUJLHYCIMQOUKC-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/29—Titanium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Description
4., 1
SPECIFICATION
POWDER COATED WITH SPARINGLY SOLUBLE ULTRAVIOLET LIGHT ABSORBER FIELD OF THE INVENTION The present invention relates in general to powder coated with a sparingly soluble ultraviolet light absorber and particularly to powder coated with a sparingly soluble ultraviolet light absorber which can contain a high concentration of a sparingly soluble ultraviolet light absorber distributed homogeneously in the base agent,, has superior stability over time and a high ultraviolet light protection effect.
BACKGROUND OF THE INVENTION Sun tanning of the skin to a brown or light brown color is primarily done by the younger generations as an expression of healthy beauty or fashion and there are many people who want to be actively sun tanned. They apply a cosmetic on the whole body and expose the skin to intense sunlight. However, recently awareness of the importance of protecting the skin from ultraviolet light has risen and cosmetics have begun to contain an ultraviolet light absorber which absorbs ultraviolet light (wavelength 290-320 nm) known to cause blisters and erythema.
However, some ultraviolet light absorbers cannot exhibit their efficacy sufficiently although they have a high ultraviolet light absorption effect because the base agent can contain only a very' small amount of them due. to their very low solubility in solvents. Among them, Pong amia extract contains Pongamol which has a very strong ultraviolet light absorption effect and is expected to be useful as a ultraviolet light absorber (Japanese examined patent publication Tokko Hei 6-60092). However, its solubility is poor in all the base agents which are usually used as'a base agent for cosmetics and therefore its application as it is in cosmetics and such has been very difficult.
DISCLOSURE OF THE INVENTION Based on the aforementioned problem, the inventors conducted earnest research and discovered that a coating of a sparingly soluble ultraviolet light absorber can be formed on the surface of various kinds of powder by mixing the sparingly soluble ultraviolet light absorber with the powder in a specific manner and that, unlike the sparingly soluble ultraviolet i I ~ln-;YIq?~lnl~ light absorber itself, said powder can be added to a cosmetic base agent in a large amount and the stability over time is superior to when a non-sparingly soluble ultraviolet light absorber is added.
That is, the present invention provedes a powder coated with a sparingly soluble ultraviolet light absorber which comprises an inorganic or organic powder whose surface is coated with the sparingly soluble ultraviolet light absorber.
A preferable method of manufacturing it is to mix the melted sparingly soluble ultraviolet light absorber and inorganic powder or organic .powder while heating -and then gradually cool them to coat the surface of said powder with the sparingly soluble ultraviolet light absorber.
BRIEF EXPLANATION OF THE DRAWINGS FIG. 1 shows the ultraviolet light transmittance of the powder coated with the sparingly soluble ultraviolet light absorber of the present invention in comparison with a simple blend. FIG. 2 is an electron microscopic photograph in place of an illustration showing the powder structure of the pongamia-extract-coated sericite powder treated with the pongamia extract. FIG. 3 is an electron microscopic photograph in place of -1 i I 4 an illustration showing the powder structure of sericite powder. FIG. 4 shows the transmitted UV light spectra for cases where W/O emulsion type sunscreen agents of Example 8 and Comparative example 7 were irradiated with light of a prescribed intensity.
THE BEST MODES OF THE EMBODIMENTS The configuration of the present invention.
is described below in detail.
A sparingly soluble ultraviolet light absorber used in the present invention refers to an ultraviolet light absorber whose solubility in isopropyl myristate at -room temperature is 2% or less. The representative example of such a sparingly soluble ultraviolet light absorber is the pongamia extract. Additional.examples include 4-(3,4-dimethoxyphenylmethylene)-2, -1-propionic acid 2-ethylhexyl ester (Softshade DH), dibenzoyl methane derivatives and Chalcone derivatives.
The Pongamia extract is a solvent extract of the seeds of Karanja and its main constituent is Pongamol. Its solubility in isopropyl myristate at room temperature is approximately 1%.
Examples of the powder used in the present invention include inorganic powders such as zinc oxide, titanium oxide, kaolin, bentonite, talc, sericite lm~:n~il I 4 I) t and mica titanium, inorganic spherical powders such as spherical calcium silicate (see Japanese unexamined patent publication Tokkai Sho 54-163830), spherical silica gel (see Tokkai Sho 54-140736), spherical silica gel treated with aluminum stearate and titanium -coated polyethylene beads, organic spherical powders such as nylon powder, methacrylic ester resin powder (see Tokkai Sho 59-193901), crystalline cellulose, spherical polymethyl methacrylate powder, polyethylene beads, vinyl acetate, N-vinyl pyrolidone, 2,4-diamino -6-phenyl 1,3,5-triazine, acrylic ester, styr-divinylbenzene copolymer, ethylene-vinyl acetate copolymer, vinyl chloride-vinyl acetate copolymer and ethylene tetrafluoride.
Of these, the most preferable powders include kaolin, talc, sericite, mica titanium and titanium oxide.
The blend ratio between the powder and the sparingly soluble ultraviolet light absorber (powder /sparingly soluble ultraviolet light absorber) is 63/35-97/3 and preferably 85/15-92/8. If the amount of the ultraviolet light absorber is too small, then the amount of the coating is small and a sufficient ultraviolet light protection effect cannot be obtained when the mixture is blended into a cosmetic. This is not preferable because then another ultravi'olet light absorber has to be added during the manufacturing
I,
6 process. On the other hand, if the amount of the ultraviolet light absorber is too large, then the amount of the coating is large and the powder tends to be an unmixed-in lump of flour. This is not preferable because then dispersivility (dispersion) in the cosmetic becomes poor and homogeneous distribution of the powder in the whole cosmetic will not be achieved, resulting in an insufficient ultraviolet light protection effect.
The powder coated with the sparingly soluble ultraviolet light absorber of the present invention can be obtained by mixing the melted sparingly soluble ultraviolet light absorber and an inorganic powder or organic powder while heating and gradually cooling them to coat the surface'of said powder with the sparingly soluble ultraviolet light absorber. This method can be implemented by the mechanofusion treatment, the thermal Henshell mixer treatment, the hybridizer system treatment, etc.
The powder coated with the sparingly soluble ultraviolet light absorber of the present invention can also be obtained by crushing a sparingly soluble ultraviolet light absorber and physically coating an inorganic powder or organic powder with it by means of a mechanochemical method.
The powder coated with the sparingly soluble ultraviolet light absorber of the present invention can also be obtained by mixing a sparingly soluble ultraviolet light absorber dissolved in a solvent and an inorganic powder or organic powder while heating and gradually cooling the mixture to coat the surface of said powder with the sparingly soluble ultraviolet light absorber. However, the ultraviolet light protection effect of the obtained powder is inferior to those obtained by the former methods. This method can be implemented by a wet treatment using an organic solvent such as acetone or ethyl acetate.
The content of the powder coated with the sparingly soluble ultraviolet light absorber in a cosmetic is ,preferably 2-60 wt%, more preferably 10-40 wt%, of the total cosmetic. It is not preferable if the content of the coated powder of the present *invention is less than 2 wt% because then the ultraviolet light protection effect drastically decreases. On the other hand, it is not preferable if the content of the coated powder of the present invention is more than 60 wt% because then the ultraviolet light protection effect will not increase in proportion to the increase in the content, the effect of the cosmetic base agent itself manifests prominently, spreadability becomes poor and the film becomes thick and finally the usability becomes poor because of stickiness.
In addition to the aforementioned essential ingredients, depending on the purpose, other ingredients which are usually blended into cosmetics can be blended into the cosmetic of the .present invention as necessary within the quantitative and qualitative range which does not affect the effect of the present invention.
Examples of these ingredients include fats/oils such as olive oil, coconut oil, safflower oil, castor oil and cottonseed oil, waxes such as lanolin, jojoba oil and carnauba wax, hydrocarbon oils such as liquid paraffin, squalane and vaseline, fatty acids, alcohols, ester oils such as cetyl octanoate and isopropyl myristate, silicone oils such as dimethyl polysiloxane and methylphenyl polysiloxane, silicone resins, humectants such .as propylene glycol, dipropylene glycol, 1,3 -butylene glycol, glycerine, isoprene glycol, polyethylene glycol, hyaluronic acid, chondroitin sulfuric acid and pyrolidone carboxylic acid, antioxidants such as tocopherol, butylhydroxy anisole and dibutylhydroxytoluene, preservatives such as methyl paraben, ethyl paraben, propyl paraben and butyl paraben, powders such as mica, bentonite, kaolin, talc, mica titanium, oxybismuth chloride and silicic anhydride, pearl agents such as guanine, laminate resin pearl agents and micatitanium type pearl agents, inorganic pigments such as ultramarine blue, chrome oxide and cobalt blue, dyes such as Sudan III, Quinizarin Green SS and Quinoline Yellow, surfactants such as Span type, Tween type, POEalkyl ether type, POE-POP type, glycerine fatty acid ester type and POE glycerine fatty ester type, thickeners such as carboxyvinyl polymer, drugs such as anti-inflammatories, vitamins and hormones and perfumes.
EXAMPLES
Examples of the present invention are explained below. The present invention is not limited to these examples. The units of the blended amounts are weight percent.
1. Preparation of a powder coated with a sparingly soluble ultraviolet light absorber Preparation .example 1 (Recipe) Pongamia extract 10. 0 wt% Sericite (Seripearl) 90.0 (Preparation method) Dry method: Powder with the composition described above was mixed using a Henshell mixer. The surface of sericite, which was the core powder, was coated with the Pongamia extract by using the mechanofusion system (from Hosokawa Micron Co., Ltd.). A 10 minute treatment at a speed of 1,500 rpm was followed by a 5 minute treatment at a speed of 2,000 rpm. The treated powder was then crushed.
FIG. 2 is an electron microscopic photograph (magnification: 10,000 times) showing the powder structure of the powder coated with the pongamia extract obtained by this preparation example. FIG.
3 is an electron microscopic photograph (magnification: 10,000 times) of the raw material sericite powder.
FIG. 2 indicates that the surface of the sericite is coated with Pongamia and, as a result, the powder particles are thicker and have an uneven surface Scompared with FIG. 3.
Preparation example 2 (Recipe) Pongamia extract 10. 0 wt% Sericite (Seripearl) 90.0 (Preparation method) Wet method: Powder with the composition described i n~ i rlr .,rr ll cl~ above was made into a slurry by using an acetone solvent and the surface of sericite, which was the core powder, was coated with the Pongamia extract by using the kneader system (from Kuramochi Co., Ltd.). In the kneader system, the temperature was raised to 60 0 C, the sericite slurry with the pongamia extract dissolved in the acetone solvent was stirred and mixed for 30 minutes, and then acetone was suctioned away while the pressure was reduced. The powder was taken out, completely dried and crushed.
Preparation example 3 (Recipe) Softshage DH 10. 0 wt% Sericite (Seripearl) 90.0 (Preparation method) Preparation was carried out in the same manner as in Preparation example 1.
Comparative preparation example 1 (Recipe) 4-t-butyl-4'-methoxy-dibenzoylmethane (Parsol 1789) 10.0 wt% Sericite (Seripearl) 90.0 (Preparation method) ii -tr:~!rr Preparation was carried out in the same manner as in Preparation example 1.
2. Methods of testing the powder treated with the sparingly soluble ultraviolet. light absorber Ten wt% of the powders treated with the sparingly soluble ult.raviolet light absorbers obtained in Preparation example 1 and Preparation example 2 were dispersed in vaseline and, after a roller treatment, the transmittance was measured using an application amount of 2.0 mg/cm. The ultraviolet light transmittance was also measured in the same manner as above for a simple mixture of the pongamia extract and the powder (weight ratio: 1 The results are shown in FIG. 1. In this figure, A is Preparation example 1, B is Preparation example 2, C is the simple mixture and D is a control (sericite only).
SThis figure indicates that the powder treated with Preparation example 1 is the most superior in the ultraviolet light protection effect.
The treated powders obtained in Preparation example 1, Preparation example 3 and Comparative preparation example 1 were molded into solid foundations according to the recipes below and their ultraviolet light protection effect was measured. The results are shown in Table 1. In this table, Control 1 does not contain the treated powder. The measurement of the ultraviolet light protection effect was evaluated by a method (in vitro) which has a high correlation with the PFA value (in vivo) which is obtained by the PFA (Protection Factor of UVA) measurement which is a protection indicator of skin darkening caused by UVA as specified in the ultraviolet light special committee of the Japan Cosmetic Industry Association.
(Recipe) Treated powder Sericite Calcinated mica Synthetic mica Titanium oxide for pigments Barium sulfate Iron oxide Fine particle titanium oxide Spherical resin powder Ethyl paraben Squalane Glyceryl trioctanoate Dimethylphenyl polysiloxane Octylmethoxy cinnamate 20. 0 wt% 20.0 20. 0 7. 0 4. 0 2. 0 2. 0 3. 0 8. 0 Appropriate amount 4. 0 4. 0 3. 0 2. 0 .1 r.t t:.yfgi-fti'; Anti-oxidant Perfume Appropriate amount Appropriate amount Table 1 Treated powder PFA value Preparation example 1 6.1 Preparation example 3 Comparative preparation example 1 9.7 Control 5.1 Table 1 indicates that the PFA value of the solid foundation which uses the treated powder-of Preparation example 1 is an improvement over that of the control by approximately one.
Also, the solid foundations described above were tested for stability over time by being allowed to stand for one month under the conditions indicated in Table 2. The results are also shown in Table 2.
(Evaluation method).
0: Good A Somewhat poor S: Poor Table 2 40 °C Temperature 50 °C 37 °C 25 °C 0°C 40 C Humidified Preparation example 1 0 0 0 0 0 Preparation example 3 0 0 0 0 0 Comparative preparation x A\ x A\ x example 1 Control 0 0 0 0 0 In terms of stability over time, the treated powder of Comparative preparation example 1 reacted with iron oxide in the foundation and turned into a chelate compound, producing a red color. On the other hand, the treated powders of Preparation example 1 and Preparation example 2 did not have problems in particular. This difference is believed to be due to the sparingly soluble characteristics and the structure of the compound.
Recipe examples of a cosmetic which uses the powder treated with the sparingly soluble ultraviolet light absorber Example 1 Solid powder foundation Mice treated with silicone 20. 0 wt% i 1 rn- r I i r.
(2) (3) (4) (6) Sericite 21.2 Titanium oxide for pigments 11.0 Fine particle titanium oxide Iron oxide Sericite coated with pongamia extract (7) (8) (9) (10) (11) (12) (13) (14) (15) Spherical resin powder Ethyl paraben Lanolin Squalane Liquid paraffin Dimethylpolysiloxane Sorbitan sesqui isostearate Octylmethoxy cinnamate Antioxidant 0 5. 0 0. 3 4. 0 4. 0 3. 0 1. 0 3. 0 Appropriate amount (Preparation method) After homegeneously mixing the powder portion with a Henshell mixer, the oil portion (9) was dripped into it and mixed with the Henshell mixer. The mixture was then crushed with a pulverizer, placed on an in.ner dish and pressure-molded to obtain a solid foundation.
The obtained solid powder foundation exhibited an in vivo PFA (n=10) of 8.75± 1.72 and an in vitro PFA of The in vivo PFA (n=10) stands for the PFA value measured using ten subjects with the method according to "Specifications for UVA prevention effect measurements by the Japan Cosmetic Industry Association" (effective on January 1, 1996) stipulated by the technical committee of the Japan Cosmetic Industry Association.
Comparative example 1 Solid powder foundation Mice treated with silicone 20.0 wt% Sericite 41.2 Titanium oxide for pigments 11. 0 Fine particle titanium oxide Iron oxide Sericite coated with pongamia extract Spherical resin powder Ethyl paraben Lanolin Squalane (11) Liquid paraffin (12) Dimethylpolysiloxane (13) Sorbitan sesqui isostearate (14) Octylmethoxy cinnamate 5. 0 0. 3 4. 0 4. 0 3. 0 1. 0 0. 3. 0 Antioxidant Appropriate amount (Preparation method) Preparation was carried out in the same manner as in Example 1.
The obtained.solid powder foundation exhibited an in vivo PFA (n=10) of 6.75± 1.75 and an in vitro PFA of 6. 1.
Example 2 Oil based stick foundation Carnauba wax 1. 5 wt% Aristwax 4. 0 Octylmethoxy cinnamate Squalane 30. 0 Liquid paraffin 12. 0 Kaolin Kaolin coated with the pongamia extract Sericite Red iron oxide Yellow oxide of iron (11) Black oxide of iron (12) Titanium oxide (13) Nylon powder (14) Paraben 0 7. 0 1. 4. 0 7. 0 5. 0 Appropriate amount (Preparation method) Portion were heated and dissolved.
To this, portion thoroughly mixed and crushed, were added and mixed while the mixture was stirred. The mixture was then ground and crushed with a colloid mill. After deaeration, the mixture was poured into a container at 70 0 C and cooled.
The obtained oil based stick foundation exhibited an in vitro PFA of 10.7.
Comparative example 2 Oil based stick foundation Carnauba wax 1. 5 w t% Aristwax Octylmethoxy cinnamate Squalane 30.0 Liquid paraffin 12.0 Kaolin 20.0 Kaolin coated with the pongamia extract Sericite Red iron oxide Yellow oxide of iron (11) Black oxide of iron (12) Titanium oxide 7. 0 (13) Nylon powder (14) Paraben Appropriate amount (Preparation method) Preparation was carried out in the same manner as in Example 2.
The obtained oil based stick foundation exhibited an in vitro PFA of 7.8.
Example 3 O/W type emulsified sunscreen cream Stearic acid 2.0 wt% Propylene glycol monostearate 2. 0 Cetanol 2. Liquid lanolin 2. 0 Liquid paraffin 5. 0 Dimethylpolysiloxane 5. 0 Purified water 64. 0 Triethanol amine 1. 0 Bentonite 0.8 (10) Propylene glycol 5. 0 (11) Paraben Appropriate amount (12) Fine particle titanium oxide coated with the pongamia extract 10.0 (13) Fine particle titanium oxide r, (Preparation method) The oil phase ingredients were heated and stirred at 70°C. The water phase was prepared by completely dissolving and then the powder portion (12) or (13) was mixed into it. The oil phase was then mixed into the water phase and emulsified with a homogenizer. The emulsion was cooled down to 30°C with a heat exchanger and then put into a container.
The obtained O/W type emulsified sunscreen cream exhibited an in vitro PFA of 5..1.
0 Comparative example 3 O/W type emulsified-sunscreen cream Stearic acid 2.0 wt% Propylene glycol monostearate Cetanol 2. Liquid lanolin 2. 0 Liquid paraffin Dimethylpolysiloxane Purified water 64. 0 Triethanol amine 1. 0 Bentonite. 0. 8 Propylene glycol (11) Paraben Appropriate amount n m r (12) Fine particle titanium oxide coated with the pongamia extract (13) Fine particle titanium oxide 10.0 (Preparation method) Preparation was carr-ied out in the same manner as in Example 3.
The obtained 0/W type emulsified sunscreen cream exhibited an in vitro PFA of Exam.ple 4 Emulsified foundation Dimethylpolysiloxane 7.0 wt% Methylphenyl polysiloxane- Decamethylcyclopentasiloxane 20. 0 Squalane Trimethylsiloxysilicate Polyoxyethylene sorbitan fatty acid ester 3. 0 Polyether modified silicone Paraben Appropriate amount Perfume Appropriate amount Fine particle t itanium oxide treated with dextrin fatty acid ester 4. 0 (11) Kaolin treate d with dextrin fatty acid ester (12) Titanium oxide treated with dextrin fatty acid ester 10. 0 (13) Iron oxide treated with dextrin fatty acid ester 2. 0 (14) Sericite treated with dextrin fatty acid ester Sericite coated with the pongamia extract .0 (16) Butylene glyco 15.0 (17) Ion exchanged water 23.9 (Preparation method) The oil phase ingredients were heated and stirred at 70 0 C. The powder ingredients were dispersed and mixed into it. The water phase ingredients (16) and (17) were added to the Smixture while emulsification with a homogenizer was conducted. The emulsion was cooled down to °C with a heat exchanger and then put into a container.
The obtained emulsified foundation exhibited an in vitro PFA of 11. 8.
Comparative example 4 Emulsified foundation Dimethylpolysiloxane 7.0 wt% Methylphenyl polysiloxane Decamethylcyclopentasiloxane 20.0 Squalane 2. 0 Trimethylsiloxysilicicate Polyoxyethylene sorbitan fatty acid ester Polyether mo-dified silicone Paraben Appropriate amount Perfume Appropriate amount Fine particle t itanium oxide treated with dextrin fatty acid ester (11) Kaolin treated with dextrin fatty acid ester (12) Titanium oxide treated with dextrin fatty acid ester 10.0 (13) Iron oxide treated with dextrin fatty acid ester 2. 0 (14) Sericite treated with dextrin fatty acid ester 0 Sericite coated with the pongamia extract (16) Butylene glycol (17) Ion exchanged water 23.9 (Preparation method) Preparation was carried out in the same manner n;nv, as in Example 4.
The obtained emulsified foundation exhibited an in vitro PFA of 8. 6.
Example 5 W/0 type emulsified solid foundation Dimethylpolysiloxane 10.0 wt% Methylphenyl polysiloxane Decamethylcyclopentasiloxane 15.0 Squalane 2. 0 Glyceryl tri (2-ethylhexanoate) Solid paraffin Carn.auba wax Polyoxyethylene sorbitan fatty acid ester Polyether modified silicone Fine particle titanium oxide treated with silicone resin 6. 0 (11) Titanium oxide treated with silicone resin 2. 0 (12) Iron oxide treated with silicone resin (13) Sericite treated with silicone resin 18. 0 (14) Spherical acrylic resin powder coated with the pongamia extract 12. 0 Butylene glycol (16) Paraben (17) Ion exchanged water 5. 0 Appropriate amount Balance (Preparation method) The oil phase ingredients were heated and stirred at 90C The powder ingredients were dispersed and mixed into it. The water phase ingredients were added to the mixture while emulsification with a homogenizer was conducted.
The emulsion was put into a container.
The obtained W/O type emulsified solid foundation exhibi.ted an in vitro PFA of 6. 3.
Comparative example 5 W/0 type emulsified solid foundation Dimethylpolysiloxane 10.0 wt% Methylphenyl polysiloxane 5. 0 Decamethylcyclopentasiloxane 15.0 Squalane Glyceryl tri (2-ethylhexanoate) Solid paraffin Carnauba wax Polyoxyethylene sorbitan fatty acid ester Polyether modified silicone Fine particle titanium oxide treated with silicone resin (11) Titanium oxide treated with silicone resin 2. 0 (12) Iron oxide treated with silicone resin 2. 0 (13) Sericite treated with silicone resin 18.0 (14) Spherical acrylic resin powder 12.0 (15) Butylene glycol (16) Paraben Appropriate amount (17) Ion exchanged water Balance (Preparation method) The oil phase ingredients were heated and stirred at 90C The powder ingredients were dispersed and mixed into it. The water phase ingredients were added to the mixture while emulsification.with a homogenizer was conducted.
The emulsion was put into a container.
The obtained W/0 type emulsified solid foundation exhibited an in vitro PFA of 3.9.
Example 6 White powder Talc coated with the pongamia extract (2) (3) 90.82 wt% Zinc white Aluminum-stearate-processed titanium dioxide Iron oxide Paraben Squalane Vaseline Sorbitan sesqui isostearate Antioxidant Perfume 0. 2 Appropriate amount 2. 0 2. 0. 3 Appropriate amount Appropriate amount The obtained white powder exhibited an in vitro SPF value of 7. 1 and an in vitro PFA (n=8) of 2.9.
Example 7 White powder Talc coated with the pongamia extract 82 wt% Zinc white 1. 0 Aluminum-stearate-processed titanium dioxide Iron oxide Paraben Octylmethoxy cinnamate 0. 2 Appropriate amount 2. 0 Vaseline Sorbitan sesqui isostearate Antioxidant Perfume 2. 0. 3 Appropriate amount Appropriate amount The obtained white powder exhibited an in vitro SPF value of 21.8 and an in vitro PFA (n=8) of 8. 2.
Comparative example 6 White powder Talc coated with metal soap 90.82 wt% Zinc white Aluminum-stearate-p-rocessed titanium dioxide 1. 0 Iron oxide Paraben Squalane Vaseline Sorbitan sesqui isostearate Antioxidant Perfume 0. 2 Appropriate amount 2. 0 2. 0. 3 Appropriate amount Appropriate amount The obtained white powder exhibited an in vitro SPF value of 13.2 and an in vitro PFA (n=8) of 7. Example 8 W/O type emulsified sunscreen agent Liquid paraffin 5.0 wt% Octylmethoxy cinnamate Decamethyl pentasiloxane 17.95 Polyether modified silicone Aluminum-stearate-processed titanium dioxide Talc coated with the pongamia extract 18.0 Butylene glycol Paraben Appropriate amount Smectite 0.7 Dispersing agent (11) Ion exchanged water Balance The obtained white powder exhibited an in vitro PFA of 1.2.
Comparative example 7 W/0 type emulsified sunscreen agent Liquid paraffin 5.0 wt% Octylmethoxy cinnamate 7. Decamethyl pentasiloxane 17.95 Polyether modified silicone Aluminum-stearate-processed titanium dioxide Talc coated with metal soap 18.0 Butylene glycol Paraben Appropriate amount Smectite 0.7 Dispersing agent (11) Ion exchanged water Balance The obtained white powder exhibited an in vitro PFA of 4.3.
The W/0 emulsified sunscreen agents of Example 8 and Comparative-example 7 were applied on tapes (product name: "Transpore" from 3M Co., Ltd.) and they were irradiated with a 150 W Xe arc lamp with a constant intensity. The transmitted UV light was Sdetected with a spectroradio meter. The in vivo FPA was calculated based on the spectra. The spectra are shown in FIG. 4.
INDUSTRIAL APPLICABILITY OF THE INVENTION As described thus far, the powder treated with the sparingly soluble ultraviolet light absorber of the present invention allows the sparingly soluble ultraviolet light absorber to be blended in a high ~Y---rtlnr~~ 32 concentration in the system and to be blended homogeneously in the base agent, and moreover, the cosmetic which contains the powder treated with the sparingly soluble ultraviolet light absorber of the present invention exhibits superior stability over time.
Claims (8)
1. Powder coated with a sparingly soluble (as herein defined) ultraviolet light absorber which is prepared by coating the surface of inorganic powder or organic powder with the sparingly soluble ultraviolet light absorber, said sparingly soluble ultraviolet light absorber comprising a pongamia extract, pongamol, 4-(3,4- acid 2-ethylhexyl ester, a dibenzoylmethane derivative or a chalcone derivative.
2. Powder coated with the sparingly soluble ultraviolet light absorber of claim 1 wherein the ultraviolet light absorber is a pongamia extract.
3. A power-containing cosmetic which contains the powder coated with the sparingly soluble ultraviolet light absorber of claim 1 or 2.
4. A method of manufacturing powder coated with a sparingly soluble (as herein defined) ultraviolet light absorber in which the melted sparingly soluble ultraviolet light absorber and an inorganic or organic powder are mixed while heating and then gradually cooled to coat the surface of said powder with the sparingly soluble 20 ultraviolet light absorber, said sparingly soluble ultraviolet light absorber comprising *oo. a pongamia extract, pongamol, 4-(3,4-dimethoxyphenylmethylene)-2,5- dioxoimidazolidine-1-propionic acid 2-ethylhexyl ester, a dibenzoylmethane derivative or a chalcone derivative.
5. A method of manufacturing powder coated with a sparingly soluble (as herein defined) ultraviolet light absorber in which the sparingly soluble ultraviolet light absorber is adsorbed to or made to coat the surface of an inorganic powder or organic powder using a mechanochemical method, said sparingly soluble ultraviolet light absorber comprising a pongamia extract, pongamol, 4-(3,4-dimethoxyphenyl- methylene)-2,5-dioxoimidazolidine-l-propionic acid 2-ethylhexyl ester, a dibenzoylmethane derivative or a chalcone derivative.
6. A powder according to claim 1 or 2, substantially as described herein and with reference to any one of Preparation Examples 1 to 3.
7. A powder-containing cosmetic according to claim 3, substantially as described herein and with reference to any one of Examples 1 to 8.
8. A method according to claim 4 or 5, substantially as described herein and with reference to any one of Preparation Examples 1 to 3. Dated this 6t day of February, 2001. SHISEIDO COMPANY LTD By its Patent Attorneys MADDERNS *o *oo o0
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25780996 | 1996-09-06 | ||
| JP8-257809 | 1996-09-06 | ||
| PCT/JP1997/003149 WO1998009610A1 (en) | 1996-09-06 | 1997-09-08 | Powder coated with sparingly soluble ultraviolet absorber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4135997A AU4135997A (en) | 1998-03-26 |
| AU731841B2 true AU731841B2 (en) | 2001-04-05 |
Family
ID=17311426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU41359/97A Ceased AU731841B2 (en) | 1996-09-06 | 1997-09-08 | Powder coated with sparingly soluble ultraviolet light absorber |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6080430A (en) |
| EP (1) | EP0860163A1 (en) |
| KR (1) | KR20000064274A (en) |
| AU (1) | AU731841B2 (en) |
| TW (1) | TW482681B (en) |
| WO (1) | WO1998009610A1 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1200039B1 (en) | 1999-07-20 | 2006-06-07 | Beiersdorf AG | Emulsifier-free finely dispersed water-in-oil-type systems |
| DE19939835A1 (en) * | 1999-08-21 | 2001-02-22 | Beiersdorf Ag | Hydrous cosmetic or pharmaceutical pens |
| KR20040052506A (en) * | 2001-05-30 | 2004-06-23 | 노프 코포레이션 | Detergent composition for dry cleaning |
| DE10140538A1 (en) * | 2001-08-17 | 2003-03-06 | Beiersdorf Ag | Cosmetic or dermatological compositions useful for treating inflammatory skin conditions and dry skin comprise a Pongamia pinnata extract |
| JP3596534B2 (en) * | 2002-03-14 | 2004-12-02 | 富士ゼロックス株式会社 | Emulsified cosmetic |
| JP2004217621A (en) * | 2002-12-27 | 2004-08-05 | Shiseido Co Ltd | Oily skin lotion |
| JP2008115270A (en) * | 2006-11-02 | 2008-05-22 | Shiseido Co Ltd | Composite powder and method for producing the same |
| JP2012121810A (en) * | 2009-02-26 | 2012-06-28 | Tayca Corp | Organic compound composite powder having ultraviolet absorbing ability, method for producing the same, and cosmetic preparation containing the same |
| JP5908699B2 (en) * | 2011-10-31 | 2016-04-26 | 富士フイルム株式会社 | Cosmetics |
| FR3001150B1 (en) * | 2013-01-24 | 2015-07-10 | Jean-Noel Thorel | ALTERNATIVE PROTECTION SYSTEM AGAINST UV AND FREE RADICALS |
| UY38401A (en) * | 2018-10-04 | 2020-04-30 | Terviva Bioenergy Inc | PONGAMIA COMPOSITIONS, ITS PREPARATION AND ANALYSIS METHODS AND THEIR USES |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03200721A (en) * | 1989-12-27 | 1991-09-02 | Riyuuhoudou Seiyaku Kk | Composite-type ultraviolet absorber |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4801445A (en) * | 1985-07-29 | 1989-01-31 | Shiseido Company Ltd. | Cosmetic compositions containing modified powder or particulate material |
| US5000945A (en) * | 1986-04-22 | 1991-03-19 | Ajinomoto Co., Inc. | Method of stabilizing a UVB absorbing compound, a stabilized UV absorber, and a cosmetic composition containing the same |
| GB8925473D0 (en) * | 1989-11-10 | 1989-12-28 | Unilever Plc | Sunscreen compositions |
| JP3542665B2 (en) * | 1995-07-07 | 2004-07-14 | 株式会社資生堂 | Anti-aging skin external preparation, collagen cross-linking inhibition skin external preparation and anti-ultraviolet skin external preparation |
-
1997
- 1997-09-06 TW TW086112891A patent/TW482681B/en not_active IP Right Cessation
- 1997-09-08 AU AU41359/97A patent/AU731841B2/en not_active Ceased
- 1997-09-08 KR KR1019980702499A patent/KR20000064274A/en not_active Abandoned
- 1997-09-08 US US09/068,110 patent/US6080430A/en not_active Expired - Fee Related
- 1997-09-08 WO PCT/JP1997/003149 patent/WO1998009610A1/en not_active Ceased
- 1997-09-08 EP EP97939211A patent/EP0860163A1/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03200721A (en) * | 1989-12-27 | 1991-09-02 | Riyuuhoudou Seiyaku Kk | Composite-type ultraviolet absorber |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4135997A (en) | 1998-03-26 |
| WO1998009610A1 (en) | 1998-03-12 |
| US6080430A (en) | 2000-06-27 |
| TW482681B (en) | 2002-04-11 |
| EP0860163A1 (en) | 1998-08-26 |
| KR20000064274A (en) | 2000-11-06 |
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